Hi nathan, your games do not contain buildNumber inside the pdxinfo file, buildNumber should be a numeric value that increases with each new update. The playdate uses this buildNumber when sideloading game to determine if a new update was available or not and download the new version.
Because this is ommited in your (new) version, when i sideload the new 1.4 version, and having version 1.3 already installed, my playdate does not download the new 1.4 after sideloading it.
It is not enough to update the version number only as this is not used to determine if an update is available by playdate or not
Search for buildNumber on this page, it explains it :